You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-06-10 21:21:54 UTC
HMDB IDHMDB00729
Secondary Accession NumbersNone
Metabolite Identification
Common NameAlpha-Hydroxyisobutyric acid
DescriptionAlpha-Hydroxyisobutyric acid is a metabolite of methyl tert-butyl ether (MTBE). MTBE may be obtained through environmental exposure. MTBE is rapidly eliminated from the body, mainly through expired air as the unchanged compound. MTBE is to some extent metabolised to t-butyl alcohol (TBA) and formaldehyde and oxidised to 2-methyl-1,2-propanediol and a-hydroxy isobuturic acid. Alpha-Hydroxyisobutyric acid has been used as an arial bactericide.
Structure
Thumb
Synonyms
ValueSource
2-Hydroxy-2-methylpropionic acidChEBI
2-Hydroxy-2-methylpropionsaeureChEBI
2-Methyl-2-hydroxypropanoic acidChEBI
2-Methyl-2-hydroxypropionsaeureChEBI
2-Methyllactic acidChEBI
Acetonic acidChEBI
Acide 2-hydroxy-2-methylpropanoiqueChEBI
acido 2-Hidroxi-2-metilpropionicoChEBI
alpha-Hydroxy-alpha-methylpropanoic acidChEBI
alpha-Hydroxy-alpha-methylpropionic acidChEBI
alpha-Hydroxyisobutanoic acidChEBI
alpha-Hydroxyisobutyric acidChEBI
HIBAChEBI
Hydroxydimethylacetic acidChEBI
2-Hydroxy-2-methylpropionateGenerator
2-HydroxyisobutyrateGenerator
2-Methyl-2-hydroxypropanoateGenerator
2-MethyllactateGenerator
AcetonateGenerator
a-Hydroxy-a-methylpropanoateGenerator
a-Hydroxy-a-methylpropanoic acidGenerator
alpha-Hydroxy-alpha-methylpropanoateGenerator
α-hydroxy-α-methylpropanoateGenerator
α-hydroxy-α-methylpropanoic acidGenerator
a-Hydroxy-a-methylpropionateGenerator
a-Hydroxy-a-methylpropionic acidGenerator
alpha-Hydroxy-alpha-methylpropionateGenerator
α-hydroxy-α-methylpropionateGenerator
α-hydroxy-α-methylpropionic acidGenerator
a-HydroxyisobutanoateGenerator
a-Hydroxyisobutanoic acidGenerator
alpha-HydroxyisobutanoateGenerator
α-hydroxyisobutanoateGenerator
α-hydroxyisobutanoic acidGenerator
a-HydroxyisobutyrateGenerator
a-Hydroxyisobutyric acidGenerator
alpha-HydroxyisobutyrateGenerator
α-hydroxyisobutyrateGenerator
α-hydroxyisobutyric acidGenerator
HydroxydimethylacetateGenerator
(CH3)2cohcoohHMDB
2-Hydroxy-2-methylpropanoateHMDB
2-Hydroxy-2-methylpropanoic acidHMDB
a-HIBHMDB
alpha-HIBHMDB
HydroxyisobutyrateHMDB
L-2-MethyllactateHMDB
L-2-Methyllactic acidHMDB
Chemical FormulaC4H8O3
Average Molecular Weight104.1045
Monoisotopic Molecular Weight104.047344122
IUPAC Name2-hydroxy-2-methylpropanoic acid
Traditional Nameacetonate
CAS Registry Number594-61-6
SMILES
CC(C)(O)C(O)=O
InChI Identifier
InChI=1S/C4H8O3/c1-4(2,7)3(5)6/h7H,1-2H3,(H,5,6)
InChI KeyInChIKey=BWLBGMIXKSTLSX-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassAlpha hydroxy acids and derivatives
Direct ParentAlpha hydroxy acids and derivatives
Alternative Parents
Substituents
  • Alpha-hydroxy acid
  • Tertiary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Toxin/Pollutant
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point82.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.36HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility378.0 mg/mLALOGPS
logP-0.37ALOGPS
logP-0.039ChemAxon
logS0.56ALOGPS
pKa (Strongest Acidic)3.95ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity23.55 m3·mol-1ChemAxon
Polarizability9.87 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00e9-8900000000-2d2298731d2c1ce975ffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0zfr-8900000000-b51c12e744025b833f31View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-9100000000-0d72fcffff267d7bc980View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0zfs-9400000000-b3b27a9cc8fd4ebe9eb1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0a4l-9000000000-bb87a50521380a4f04c0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0900000000-09121cf499d55d5656acView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0pb9-9600000000-3394a5ec4ff4ff576fcdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9000000000-5fc3362d72c467fb6197View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-052f-9000000000-3de5183bd97ccc5072c8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-d524fab140880c782425View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0a4i-0900000000-1aadb4e9ee70b665d435View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-0900000000-591fd3d7ad484dd6f1ffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0udi-0900000000-69f23830b20d34978bedView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-8900000000-f40f4783e4b817b45a70View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9100000000-28ad10690e6680bd4046View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-0a3b71647acebd936a7eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1900000000-7f058188704b24bc8ceeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2900000000-40bbfa4d36a4c19902c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-237ae993c0cc1090dd96View in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified8.2 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified7.0 (0.0-9.0) uMAdult (>18 years old)BothNormal details
SalivaDetected and Quantified9.00 +/- 2.95 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified2.9 (1.3-4.6) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified4.4-7.4 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified7.821 +/- 3.811 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified3.80 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Shaykhutdinov RA,...
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.1 (0.1-3.8) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified6.2 (3.8-14.1) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified5.5 (2.9-10.3) umol/mmol creatinineAdolescent (13-18 years old)Both
Normal
details
UrineDetected and Quantified<50 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified7.9 (3.7-19.5) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified0.1 (0.1-8.2) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified4.4-7.6 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified3.8 (1.7-5.9) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified13.322 +/- 5.638 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Lung cancer
details
UrineDetected and Quantified9.37 +/- 5.223 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified5.0 (0.0-8.0) umol/mmol creatinineNot SpecifiedBothLung cancer details
UrineDetected and Quantified11.83 +/- 4.351 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified12.057 +/- 6.013 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease References
Lung Cancer
  1. Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2008 Oct 25. [18953024 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022207
KNApSAcK IDNot Available
Chemspider ID11181
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00729
Metagene LinkHMDB00729
METLIN ID3750
PubChem Compound11671
PDB IDNot Available
ChEBI ID50129
References
Synthesis ReferenceVogl, O. Synthesis of a-hydroxyisobutyric acid from isobutylene. Journal of Organic Chemistry (1958), 23 1488-9.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [8087979 ]
  2. Benson JM, Barr EB, Krone JR: MTBE inhaled alone and in combination with gasoline vapor: uptake, distribution, metabolism, and excretion in rats. Res Rep Health Eff Inst. 2001 May;(102):73-94; discussion 95-109. [11504149 ]
  3. NTP Toxicology and Carcinogenesis Studies of Isobutene (CAS No. 115-11-7) in F344/N Rats and B6C3F1 Mice (Inhalation Studies). Natl Toxicol Program Tech Rep Ser. 1998 Dec;487:1-230. [12563344 ]
  4. Shigematsu Y, Sudo M, Momoi T, Inoue Y, Suzuki Y, Kameyama J: Changing plasma and urinary organic acid levels in a patient with isovaleric acidemia during an attack. Pediatr Res. 1982 Sep;16(9):771-5. [7133811 ]